Help in getting a second sneak attack

[Krachek]

The Sentinel feat can allow extra sneak attack.
Otherwise you can nerf SS and GWM.

 

[5ekyu]

I would prefer to retain the illusion.

Overtly changing the core rules means accepting they are lacking.

If at all possible I would like to handle this by placing a magic item as loot or in shoppe.

Seems like keep changing objectives.

While admiting the rules are the problem you refuse to accept changing them.

While admiting the player is unhappy ypu claim their is some illusion of things being ok even tho you admit its not, due to your group focus comvat etc and not seeing skills as balancing out the combat.

All ok.

But then also dismiss multiclass optimizations cuz player does not want to optimize that wzy, or you dont.

Hard to tell how much this is an actual game problem vs an agenda to keep throwing in enough dismissals to make some case.

Add the Ring of Zapp.
Only worls for players named abc playing rogues nsmed def and it adds jkl damage to their attacks.

Now fill in the names and numbers to reach the benchmarks u want. But be ready to pull it once "the player" decides maybe optimizing a bit is ok if keeping up with optimizers is important instead of hoping GM hands him an item is the key.

Now, again, since my players are not idiots, i prefer to "change bad rules" by "changing rules" not by inseting items under my own illusion they wont see thru that illusion.

But each game is different, so, whatever works.

 

[Ancalagon]

I agree, so I suggested some items that would benefit the rogue by applying the poison. As long as you tailor them to support the rogue, it shouldn't be a problem. As soon as you hit with an attack the poison is used up. The poison can have a time associated with it. After being coated on a normal weapon, it dissipates after 10 minutes.

The rogue's weapons can have special grooves that hold the poison. The poison requires a minimum intelligence to apply correctly or you risk poisoning yourself. It might be possible for a fighter to get one use of a poison in the first attack of combat, but not repeated uses through the encounter.

ooor a dagger of venom?

Maybe if I say it three times

 

[Thurmas]

ooor a dagger of venom?

Maybe if I say it three times

You can say it as many times as you like, but it hardly achieves what the OP was asking. A DC 15 check to do 2d8 extra damage once per day is hardly going to give the boost in damage he was asking for.

 

[Ancalagon]

You can say it as many times as you like, but it hardly achieves what the OP was asking. A DC 15 check to do 2d8 extra damage once per day is hardly going to give the boost in damage he was asking for.

It's once a day!?! Well that's mediocre...

 

[Saeviomagy]

So, to paraphrase, the problem is:

"I have a player who gets upset when he doesn't do as much damage as the other players, but he wants to do so without putting in any effort, and while in an environment that is being made hostile by the other players, in a game where nothing except combat matters and resources are never taxed."

And from the sounds of things, effort includes:
Multiclassing, dual wielding, taking feats, abusing opportunity attacks, coming up with cunning plans etc.

The base rogue class does a couple of things extremely well:
1. They don't expend resources, so if your adventuring days are so short that (say) the barbarian can always be raging, or the sorcerer never needs to conserve spell slots, then they are not going to keep up.
2. They do skill checks. The rogue is going to need to put some effort into lining up skill checks that will swing combats, and the DM is going to need to let that sort of thing happen. "I throw a dagger for... 17 points of damage. Then I use my bonus action on an automatic success on a DC 20 disable device check to collapse the roof of the tunnel, burying most of the enemy force" is the sort of thing that is possible for a rogue, but ineffective for anyone else (most classes would get a 50/50 shot at the skill check at best, and need to spend a full action for each attempt).

I would advise NOT hiding in the middle of combat BTW. Rogues only have slightly fewer hit points than a fighter, and only slightly less AC than one clad in full plate. They then halve the damage on one attack per round and often take reduced damage from spells. They should be far from squishy. Although my guess is that your rogue has done something silly like dump constitution and then wonder why he has so few hit points.

 

[CapnZapp]

Here's one possible solution

Panther Strike Bracers (requires attunement)
Panther strike bracers allow you to answer an unsuccessful melee attack against you with an unexpected riposte. Spend your reaction to make an opportunity attack immediately after an enemy
has missed you with a melee attack. If this opportunity attack also misses, the bracers can't be used
again until you take a short rest.

I modeled them after Counterstrike Bracers from d20.

 

[Satyrn]

Here's one possible solution

Panther Strike Bracers (requires attunement)
Panther strike bracers allow you to answer an unsuccessful melee attack against you with an unexpected riposte. Spend your reaction to make an opportunity attack immediately after an enemy
has missed you with a melee attack. If this opportunity attack also misses, the bracers can't be used
again until you take a short rest.

I modeled them after Counterstrike Bracers from d20.

That has the same problem as the dagger of venom to nearly the same degree - it may allow one single use in a day, probably just a few.

 

[TheSword]

Consider giving injury poisons from the DMG as treasure or the components for crafting them. If I recall correctly they last a minute after being applied which is normally more than enough to last an encounter. Dealing extra poison damage on every hit.

As an aside, your rogue is crazy if they aren’t two weapon fighting in melee against all but the strongest enemies (to get that second chance at sneak if they miss on the first). If the for is that strong, then stand back and shoot a short bow for the same effect and let tougher foes take the heat. The rogue should adapt to the foe, which other characters may not be so effective at.

 

[Tony Vargas]

I would prefer to retain the illusion.

Overtly changing the core rules means accepting they are lacking.

If at all possible I would like to handle this by placing a magic item as loot or in shoppe.

Seems like keep changing objectives.

Really?

what canon or even semi-canon ways are available to me to introduce a magic item that helps with this situation, drawing from both 5e and 3e magic items.

Sounds like the same objective, to me.

And a very reasonable one, exactly the kind of thing a 5e DM is Empowered to do. Magic items in 5e are specifically intended to make the lucky character with one "just better." The DM finds a character isn't good enough? Boom, magic item, and he's better, just like that.